DE1118789B - Verfahren zur Herstellung von 1, 3, 5-Triazinderivaten - Google Patents
Verfahren zur Herstellung von 1, 3, 5-TriazinderivatenInfo
- Publication number
- DE1118789B DE1118789B DEI15546A DEI0015546A DE1118789B DE 1118789 B DE1118789 B DE 1118789B DE I15546 A DEI15546 A DE I15546A DE I0015546 A DEI0015546 A DE I0015546A DE 1118789 B DE1118789 B DE 1118789B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- triazine
- formula
- mixture
- filtered
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 12
- 125000003363 1,3,5-triazinyl group Chemical class N1=C(N=CN=C1)* 0.000 title claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 229940123208 Biguanide Drugs 0.000 claims description 6
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 239000000203 mixture Substances 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000007787 solid Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- -1 z. B. Hydrochloride Chemical class 0.000 description 14
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 229910052708 sodium Inorganic materials 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical compound NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 4
- VXMGBSXIKBWFBU-UHFFFAOYSA-N n-methyl-1,3,5-triazin-2-amine Chemical compound CNC1=NC=NC=N1 VXMGBSXIKBWFBU-UHFFFAOYSA-N 0.000 description 4
- 150000000182 1,3,5-triazines Chemical class 0.000 description 3
- PEHJTVMOGGJPJM-UHFFFAOYSA-N 6-(chloromethyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(CCl)=N1 PEHJTVMOGGJPJM-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XGESZDIYTMNBCS-UHFFFAOYSA-N 2-n,4-n-dimethyl-1,3,5-triazine-2,4-diamine Chemical compound CNC1=NC=NC(NC)=N1 XGESZDIYTMNBCS-UHFFFAOYSA-N 0.000 description 2
- CFDIKCANOYSMES-UHFFFAOYSA-N 6-(bromomethyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(CBr)=N1 CFDIKCANOYSMES-UHFFFAOYSA-N 0.000 description 2
- DKUHPVHMNNMUHU-UHFFFAOYSA-N 6-(iodomethyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(CI)=N1 DKUHPVHMNNMUHU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229940075930 picrate Drugs 0.000 description 2
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical class [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 2
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000007944 thiolates Chemical class 0.000 description 2
- DQUDKYAOQDREIB-UHFFFAOYSA-N 1,3,5-triazin-1-ium;chloride Chemical compound Cl.C1=NC=NC=N1 DQUDKYAOQDREIB-UHFFFAOYSA-N 0.000 description 1
- KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 description 1
- JLPWQEHTPOFCPG-UHFFFAOYSA-N 1-(diaminomethylidene)-2-methylguanidine Chemical compound CN=C(N)N=C(N)N JLPWQEHTPOFCPG-UHFFFAOYSA-N 0.000 description 1
- FKPUYTAEIPNGRM-UHFFFAOYSA-N 1-(diaminomethylidene)guanidine;hydron;chloride Chemical compound [Cl-].N\C([NH3+])=N/C(N)=N FKPUYTAEIPNGRM-UHFFFAOYSA-N 0.000 description 1
- PUEDDLZNHFILHG-UHFFFAOYSA-N 2-(diazomethyl)-1,3,5-triazine Chemical class [N+](=[N-])=CC1=NC=NC=N1 PUEDDLZNHFILHG-UHFFFAOYSA-N 0.000 description 1
- VPSXHKGJZJCWLV-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(1-ethylpiperidin-4-yl)oxypyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)OC1CCN(CC1)CC VPSXHKGJZJCWLV-UHFFFAOYSA-N 0.000 description 1
- RVBUZBPJAGZHSQ-UHFFFAOYSA-N 2-chlorobutanoic acid Chemical compound CCC(Cl)C(O)=O RVBUZBPJAGZHSQ-UHFFFAOYSA-N 0.000 description 1
- AKWJBSDLSFROSK-UHFFFAOYSA-N 2-methyl-1-(n'-methylcarbamimidoyl)guanidine Chemical compound CNC(=N)NC(=N)NC AKWJBSDLSFROSK-UHFFFAOYSA-N 0.000 description 1
- YPACHCKIUZUMRA-UHFFFAOYSA-N 2-n,6-dimethyl-1,3,5-triazine-2,4-diamine Chemical class CNC1=NC(C)=NC(N)=N1 YPACHCKIUZUMRA-UHFFFAOYSA-N 0.000 description 1
- GFKADPKWCIVAPO-UHFFFAOYSA-N 4-piperidin-1-yl-1,3,5-triazin-2-amine Chemical compound NC1=NC=NC(N2CCCCC2)=N1 GFKADPKWCIVAPO-UHFFFAOYSA-N 0.000 description 1
- VXNCYCIWEODIAX-UHFFFAOYSA-N 6-(chloromethyl)-2-N-methyl-1,3,5-triazine-2,4-diamine Chemical compound ClCC1=NC(=NC(=N1)N)NC VXNCYCIWEODIAX-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FMYMNBKECYNCPZ-UHFFFAOYSA-N C(C)C1=NC(=NC(=N1)NC)N Chemical compound C(C)C1=NC(=NC(=N1)NC)N FMYMNBKECYNCPZ-UHFFFAOYSA-N 0.000 description 1
- ORLAUUZWYITUIW-UHFFFAOYSA-N C(C)OP(=O)(SCC1=NC(=NC(=N1)N)N)OCC Chemical compound C(C)OP(=O)(SCC1=NC(=NC(=N1)N)N)OCC ORLAUUZWYITUIW-UHFFFAOYSA-N 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- XSEUMFJMFFMCIU-UHFFFAOYSA-N buformin Chemical compound CCCC\N=C(/N)N=C(N)N XSEUMFJMFFMCIU-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- MFFXVVHUKRKXCI-UHFFFAOYSA-N ethyl iodoacetate Chemical compound CCOC(=O)CI MFFXVVHUKRKXCI-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/65031—Five-membered rings having the nitrogen atoms in the positions 1 and 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
- C07F9/6521—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6524—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having four or more nitrogen atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB33358/57A GB899701A (en) | 1957-10-25 | 1957-10-25 | New phosphorus-containing organic compounds |
| GB13939/59A GB913334A (en) | 1957-10-25 | 1959-04-23 | New organo-phosphorus s-triazine compounds and their use as pesticides |
| GB13940/59A GB932388A (en) | 1959-04-23 | 1959-04-23 | New thiophosphoric acid esters and pesticidal compositions containing them |
| GB16716/59A GB917420A (en) | 1957-10-25 | 1959-05-15 | Organo-polymers s-triazine derivatives and pesticidal compositions containing them |
| GB3687864 | 1964-01-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1118789B true DE1118789B (de) | 1961-12-07 |
Family
ID=31950830
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEJ17863A Pending DE1245206B (de) | 1957-10-25 | 1958-10-23 | Insektenbekaempfungsmittel |
| DEI15546A Pending DE1118789B (de) | 1957-10-25 | 1958-10-23 | Verfahren zur Herstellung von 1, 3, 5-Triazinderivaten |
| DEJ18006A Pending DE1132560B (de) | 1957-10-25 | 1960-04-22 | Verfahren zur Herstellung von 1, 3, 5-Triazinderivaten |
| DEJ18119A Pending DE1159462B (de) | 1957-10-25 | 1960-05-13 | Verfahren zur Herstellung von s-Triazinderivaten |
| DEJ20952A Pending DE1217695B (de) | 1957-10-25 | 1960-05-13 | Insekticide Mittel mit acaricider Wirkung |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEJ17863A Pending DE1245206B (de) | 1957-10-25 | 1958-10-23 | Insektenbekaempfungsmittel |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEJ18006A Pending DE1132560B (de) | 1957-10-25 | 1960-04-22 | Verfahren zur Herstellung von 1, 3, 5-Triazinderivaten |
| DEJ18119A Pending DE1159462B (de) | 1957-10-25 | 1960-05-13 | Verfahren zur Herstellung von s-Triazinderivaten |
| DEJ20952A Pending DE1217695B (de) | 1957-10-25 | 1960-05-13 | Insekticide Mittel mit acaricider Wirkung |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US3185699A (tr) |
| BE (1) | BE572314A (tr) |
| CH (4) | CH374689A (tr) |
| DE (5) | DE1245206B (tr) |
| FR (5) | FR1219238A (tr) |
| GB (2) | GB913334A (tr) |
| NL (2) | NL103644C (tr) |
| SE (1) | SE320379B (tr) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3270031A (en) * | 1957-10-25 | 1966-08-30 | Ici Ltd | Certain tetrazolylmethyl phosphorothioates |
| US3131186A (en) * | 1962-07-19 | 1964-04-28 | American Of Cyanamid Company | Unsymmetrically substituted triazinyl alkyl phosphates |
| US3102885A (en) * | 1962-07-19 | 1963-09-03 | American Cyanamid Co | Triazinylalkyl phosphates |
| US3260719A (en) * | 1964-01-17 | 1966-07-12 | Ici Ltd | Organo-phosphorus s-triazine derivatives |
| US3336314A (en) * | 1964-12-02 | 1967-08-15 | Mobil Oil Corp | O-quinolinyl s-alkyl-alkylphos-phonodithioates |
| US3409617A (en) * | 1965-08-13 | 1968-11-05 | Wolfen Filmfab Veb | Pesticidal triazinyl phosphoric acid esters |
| US3687966A (en) * | 1970-10-29 | 1972-08-29 | Hercules Inc | O,o-di-(c1{14 c2 alkyl) s-{8 1-(c2{13 c20 acyl) hydantoin-3-yl{9 methyl phosphorthioates |
| DE2140865B2 (de) * | 1971-08-14 | 1979-10-11 | Bayer Ag, 5090 Leverkusen | 1 -Imidazolyl-methanphosphonsäureester, Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel |
| DE2431848A1 (de) * | 1974-07-02 | 1976-01-22 | Bayer Ag | Imidazolyl-(thiono)-phosphor(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide, akarizide und nematizide |
| BE863713A (fr) * | 1977-02-09 | 1978-08-07 | Smithkline Corp | Sels d'imidazole-methylphosphonium, leur procede de preparation et leurs applications |
| US4104472A (en) * | 1977-02-09 | 1978-08-01 | Smithkline Corporation | Imidazolemethylphosphonium salts |
| US4197295A (en) * | 1978-10-02 | 1980-04-08 | Stauffer Chemical Company | Pyrazole phosphates and phosphonates - insecticides |
| US4451381A (en) * | 1982-07-26 | 1984-05-29 | Diamond Crystal Salt Company | Composite plug for stake-hole of salt blocks, salt block product, and method of using same |
| AU2278183A (en) * | 1983-01-07 | 1984-07-12 | F. Hoffmann-La Roche & Co. | Pyrimidine di thiophosphate derivatives |
| CN105348324B (zh) * | 2015-12-02 | 2017-06-30 | 河南农业大学 | 含有四唑杂环的有机磷化合物及其合成方法与应用 |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2619486A (en) * | 1952-11-25 | Dialkoxyacetoguanamines | ||
| US2368451A (en) * | 1940-11-15 | 1945-01-30 | Gen Electric | Polyaminotriazine-formaldehyde resin modified with a preformed mono salt of a polyaminotriazine |
| US2354940A (en) * | 1942-10-20 | 1944-08-01 | Claude R Wickard | Fungicide |
| US2349344A (en) * | 1943-08-21 | 1944-05-23 | Nasa | Insecticide |
| BE637016A (tr) * | 1951-04-20 | 1900-01-01 | ||
| DE933627C (de) * | 1953-02-10 | 1955-09-29 | Bayer Ag | Verfahren zur Herstellung von Thiophosphorsaeureestern |
| US2843588A (en) * | 1953-02-26 | 1958-07-15 | Bayer Ag | Derivatives of thiophosphoric acid |
| US2802855A (en) * | 1953-04-27 | 1957-08-13 | Shell Dev | Carbamylalkenyl phosphoruscontaining esters |
| US2980675A (en) * | 1953-06-02 | 1961-04-18 | Degussa | Process for the production of thiophosphoric esters of symmetrical triazines |
| DE936690C (de) * | 1953-06-03 | 1955-12-22 | Degussa | Verfahren zur Herstellung von Dialkylthiophosphorsaeureestern symmetrischer Triazine |
| FR1135848A (fr) * | 1954-08-16 | 1957-05-03 | Geigy Ag J R | Agents susceptibles d'influencer la croissance des plantes |
| DE1067016B (de) * | 1954-12-04 | 1959-10-15 | Farbenfabriken Bayer Aktiengesellschaft Leverkusen-Bayerwerk | Verfahren zur Her stellung von organischen Phosphorver bmdungen |
| US2758115A (en) * | 1955-02-10 | 1956-08-07 | Bayer Ag | Derivatives of thiophosphoric acid |
| US2767194A (en) * | 1955-03-18 | 1956-10-16 | Stauffer Chemical Co | Compositions of matter |
| DE949231C (de) * | 1955-05-03 | 1956-09-13 | Bayer Ag | Verfahren zur Herstellung von chlkorierten Benzylestern der Thiol- bzw. Thionothiolphosphorsaeuren |
| BE547771A (tr) * | 1955-05-13 | |||
| US2865912A (en) * | 1956-06-05 | 1958-12-23 | Basf Ag | Process for the production of o.o-dialkylphosphoric or o.o-dialkylthionophosphoric acid esters of n-alkylol lactams |
| BE558354A (tr) * | 1956-06-15 | |||
| DE1064064B (de) * | 1956-06-15 | 1959-08-27 | Bayer Ag | Verfahren zur Herstellung von Thionophosphorsaeureestern von N-Methylolverbindungen |
| US2887432A (en) * | 1956-06-28 | 1959-05-19 | Monsanto Chemicals | Dialkoxyphosphinothioylthio-s-triazines |
| BE563003A (tr) * | 1956-10-25 | |||
| US2822364A (en) * | 1957-05-22 | 1958-02-04 | American Cyanamid Co | Novel anionic guanamine phosphonates and methods for preparing same |
| US2848451A (en) * | 1957-05-22 | 1958-08-19 | American Cyanamid Co | Polyethoxamers of novel quaternary ammonium salts and method for preparing the same |
| US2919274A (en) * | 1957-09-17 | 1959-12-29 | Sahyun Melville | Amidines |
| US2907787A (en) * | 1957-11-13 | 1959-10-06 | Friedrich W Hoffmann | Preparation of phosphono-thiono esters of 2-hydroxyethyl sulfides |
| US2893993A (en) * | 1958-06-17 | 1959-07-07 | Searle & Co | 2-aryloxyaralkyl-1, 4, 5, 6-tetrahydropyrimidines |
| US3011998A (en) * | 1958-10-17 | 1961-12-05 | Dal Mon Research Co | Condensation of aldehydes with triazinyl phosphonic esters and amides and products thereof |
| US2976207A (en) * | 1959-02-27 | 1961-03-21 | Standard Oil Co | Dihydroxy-aminotriazine insecticides |
| US2938902A (en) * | 1959-04-24 | 1960-05-31 | American Cyanamid Co | Novel pyridazinones and methods of preparing same |
-
0
- NL NL111238D patent/NL111238C/xx active
- BE BE572314D patent/BE572314A/xx unknown
- NL NL103644D patent/NL103644C/xx active
-
1958
- 1958-10-23 DE DEJ17863A patent/DE1245206B/de active Pending
- 1958-10-23 DE DEI15546A patent/DE1118789B/de active Pending
- 1958-10-24 FR FR777508A patent/FR1219238A/fr not_active Expired
- 1958-10-24 CH CH6539358A patent/CH374689A/de unknown
-
1959
- 1959-04-23 GB GB13939/59A patent/GB913334A/en not_active Expired
- 1959-05-15 GB GB16716/59A patent/GB917420A/en not_active Expired
-
1960
- 1960-04-11 US US21133A patent/US3185699A/en not_active Expired - Lifetime
- 1960-04-22 CH CH454160A patent/CH380734A/de unknown
- 1960-04-22 DE DEJ18006A patent/DE1132560B/de active Pending
- 1960-04-22 CH CH454260A patent/CH385224A/de unknown
- 1960-04-23 FR FR825170A patent/FR77659E/fr not_active Expired
- 1960-04-23 FR FR825171A patent/FR77866E/fr not_active Expired
- 1960-04-29 US US25563A patent/US3134775A/en not_active Expired - Lifetime
- 1960-05-13 DE DEJ18119A patent/DE1159462B/de active Pending
- 1960-05-13 DE DEJ20952A patent/DE1217695B/de active Pending
- 1960-05-13 CH CH551160A patent/CH380735A/de unknown
- 1960-05-16 FR FR827349A patent/FR78060E/fr not_active Expired
-
1963
- 1963-06-24 US US290196A patent/US3169964A/en not_active Expired - Lifetime
-
1964
- 1964-03-23 FR FR968354A patent/FR85612E/fr not_active Expired
-
1965
- 1965-04-21 SE SE5172/65A patent/SE320379B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR1219238A (fr) | 1960-05-16 |
| FR78060E (fr) | 1962-06-01 |
| SE320379B (tr) | 1970-02-09 |
| CH380734A (de) | 1964-08-15 |
| DE1132560B (de) | 1962-07-05 |
| BE572314A (tr) | 1900-01-01 |
| FR77659E (fr) | 1962-04-06 |
| DE1217695B (de) | 1966-05-26 |
| GB913334A (en) | 1962-12-19 |
| US3169964A (en) | 1965-02-16 |
| DE1159462B (de) | 1963-12-19 |
| FR85612E (fr) | 1965-09-17 |
| CH380735A (de) | 1964-08-15 |
| CH385224A (de) | 1964-12-15 |
| CH374689A (de) | 1964-01-31 |
| FR77866E (fr) | 1962-05-04 |
| US3134775A (en) | 1964-05-26 |
| DE1245206B (de) | 1967-07-20 |
| NL103644C (tr) | 1900-01-01 |
| NL111238C (tr) | 1900-01-01 |
| US3185699A (en) | 1965-05-25 |
| GB917420A (en) | 1963-02-06 |
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